(11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-1(10),2,4,6-tetraen-14-one

• ChemBase ID: 165636
• Molecular Formular: C18H20O2
• Molecular Mass: 268.3502
• Monoisotopic Mass: 268.14632988
• SMILES: c1c(cc2c(c1)C1=C(CC2)[C@H]2[C@](CC1)(C(=O)CC2)C)O
• Canonical SMILES: Oc1ccc2c(c1)CCC1=C2CC[C@]2([C@H]1CCC2=O)C
• InChI: InChI=1S/C18H20O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,16,19H,2,4,6-9H2,1H3/t16-,18-/m0/s1
• InChIKey: OUGSRCWSHMWPQE-WMZOPIPTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1(10),2,4,6-tetraen-14-one
• IUPAC Traditional name: (11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1(10),2,4,6-tetraen-14-one
• Synonyms: 3-Hydroxyestra-1,3,5(10),8-tetraen-17-one; Δ8-Dehydroestrone; Δ8-Isoequilin; 8,9-Dehydroestrone; Δ8,9-Dehydro Estrone

Database IDs

• CAS Number: 474-87-3
• PubChem SID: 162259769
• PubChem CID: 6451472

CALCULATED PROPERTIES

• Acid pKa: 9.550477
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.9984865
• LogD (pH = 7.4): 3.9954824
• Log P: 3.9985251
• Molar Refractivity: 79.6658 cm^3
• Polarizability: 30.673712 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dioxane
• Apperance: Off-White Solid
• Melting Point: 219-221°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D229640

A metabolite of Equilin steroid.

REFERENCES

• Beetz, T., et al.: J. Med. Chem., 25, 714 (1982)
• Thompson, J., et al.: Drug Metab. Dispos., 15, 833 (1982)
• Lupulescu, A., et al.: Cancer Invest., 13, 287 (1982)
• Baracat, E., et al.: J. Clin. Endocrinol. Metab., 84, 2020 (1982)